From Emily Ratajkowski to Olivia Wilde: A full timeline of Harry Styles’ rumoured romances

The singer was recently filmed kissing model Emily Ratajkowski

In the past few years, Harry Styles has been romantically linked to numerous celebrities, prompting ongoing speculation from fans about what his relationship status is.

Most recently, the singer made headlines when he was filmed kissing model Emily Ratajkowski while they were captured standing together on a street in Tokyo. However, it isn’t necessarily a surprise that Styles hasn’t publicly addressed the interaction, as he’s previously said that he likes to keep his sexuality and relationships private.

“I’ve never talked about my life away from work publicly and found that it’s benefited me positively,” he told Rolling Stone in August 2022. “There’s always going to be a version of a narrative, and I think I just decided I wasn’t going to spend the time trying to correct it or redirect it in some way.”

While he was romantically link to Olivia Wilde at the time of the interview, the “As It Was” singer also noted that, although he’s been photographed with different women, it hasn’t necessarily meant he was dating them.

“Sometimes people say: ‘You’ve only publicly been with women,’ and I don’t think I’ve publicly been with anyone,” he added. “If someone takes a picture of you with someone, it doesn’t mean you’re choosing to have a public relationship or something.”

Although Styles typically chooses to keep details about his romantic relationships private, it hasn’t stopped fans from speculating about his love life each time he is spotted with a fellow star. From Taylor Swift to Kendall Jenner, here’s a full timeline of Styles’ rumoured romances.

2011: Caroline Flack

The former One Direction singer was in a relationship with Caroline Flack from 2011 to 2012. At the time, the 17-year-old singer took to Twitter to share that the breakup was a “mutual decision,” as reported by BBC News. He also called Flack, who was 14 years older than him, one of the “kindest, sweetest people” that he knew.

The pair first met in 2011, when Styles and his band appeared on The X Factor while Flack was hosting the show. The former Love Island host later died by suicide at the age of 40, in April 2020.

2012: Emily Atack

Emily Atack was romantically linked to Styles in 2012, before she revealed one year later that they were never an official couple. “We were never boyfriend and girlfriend,” she said during a 2013 interview with Reveal magazine, according to Hello! “I think that’s the first time I’ve ever admitted to what it was, because I’ve always just shrugged it off before.”

She went on to describe their “short-lived thing” together. “Then we went off in our opposite directions,” she said. “It was brief, but fun, and then we moved on.”

2012 to 2013: Taylor Swift

The two musicians briefly dated between 2012 and 2013, during which they were spotted on a date in New York City. Following their split, fans speculated that some of Taylor Swift’s songs were about her ex, including “Out of the Woods” and of course, “Style”.

The pair have appeared to maintain a good friendship over the years, as they were seen talking in the crowd at the Grammy Awards in February, with photos showing them exchanging a fist bump. Swift also danced in the audience as Styles performed his hit song, “As It Was,” during the ceremony.

2013 and 2016: Kendall Jenner

The alleged couple were first spotted together in November 2013 at a restaurant in Hollywood, shortly after Styles’ split from Swift. Kendall Jenner and the singer kept their rumoured  romance underwraps, as they appeared to call things off a few months later.

However, they were seen together again in January 2016, while on board a yacht with Ellen DeGeneres and her wife, Portia de Rossi. Days later, Jenner’s older sister, Khloe Kardashian, addressed the model’s relationship with Styles and joked that they were dating.

“Do I think they’re dating? Yes,” she told Entertainment Tonight, at the time. “I don’t know if they’re like boyfriend-girlfriend…I don’t know their title. But I mean, they were in St Barts together hanging out, so to me that’s dating.”

While Jenner and Styles were seen together on multiple occasions in 2016, they never confirmed that they were in a relationship. Although they opted not to keep their romance going, they did reunite in 2019, when they both appeared on The Late Late Show to play a game of “Fill Your Guts or Spill Your Guts“ and share some of their personal secrets.

2014 to 2015: Nadine Leopold

Nadine Leopold and Styles were spotted together a few times from 2014 to 2015, including during an outing in Beverly Hills. However, they never publicly confirmed that they were dating.

2015: Sara Sampaio

Shortly after Styles’ rumoured romance with Leopold ended, he was spotted with Victoria’s Secret Angel Sara Sampaio. In June 2015, the pair were seen hugging outside of Ludlow Hotel in New York City. However, they never confirmed if they a couple or not.

2017: Tessa Ward

Styles and Tessa Ward appeared to have a brief romance, with a source claiming to Us Weekly in May 2017 that they were “really into each other”. While neither of the stars spoke out about the dating speculation, the publication also reported that they were just “casually seeing each other”.

2017 to 2018: Camille Rowe

The singer and Camille Rowe were first spotted together in July 2017, while at a Fleetwood Mac show. Days later, Styles appeared on Nick Grimshaw’s BBC 1 Radio show and was shown a picture of Rowe while hooked up to a heart rate monitor.

“I don’t know her, but I’m sure she’s a wonderful person,” he responded with a smile on his face. He then shook his head and laughed at his friend’s remark, before he jokingly added: “I hate you all so much.”

Although they didn’t publicly confirm the romance,The Sun reported in July 2018 that Rowe and Styles had broken up. During Styles’ cover story interview for Rolling Stone in 2019, his collaborator, Tom Hull, spoke about a breakup Styles had gone through, seemingly referring to the singer’s rumoured relationship with Rowe.

“He went through this breakup that had a big impact on him,” Hull said.  “I turned up on Day One in the studio, and I had these really nice slippers on. His ex-girlfriend that he was really cut up about, she gave them to me as a present - she bought slippers for my whole family. We’re still close friends with her. I thought: ‘I like these slippers. Can I wear them - is that weird?’”

He said that when Styles asked where he got the slippers, he confessed: “Oh, um, your ex-girlfriend got them for me.’ He said: ‘Whaaaat? How could you wear those?’”

Hull added: “[Styles] had a whole emotional journey about her, this whole relationship. But I kept saying: ‘The best way of dealing with it is to put it in these songs you’re writing.’”

2021 to 2022: Olivia Wilde

Styles and Olivia Wilde first met in September 2020 while on the set of their film, Don’t Worry Darling. They first sparked romance rumours in January 2021, when they were spotted holding hands at a wedding. The news came as a surprise to fans, since Wilde had separated from ex Jason Sudeikis just two months before she was seen with Styles.

During their relationship, they both addressed criticism they received from fans over their dating lives. In August 2022, Styles responded to the criticism and described Twitter as “a s***storm of people trying to be awful to people” while discussing how fame placed pressure on his close relationships.

“That obviously doesn’t make me feel good,” he told Rolling Stone. “It’s obviously a difficult feeling to feel like being close to me means you’re at the ransom of a corner of Twitter or something. I just wanted to sing. I didn’t want to get into it if I was going to hurt people like that.”

During an interview with Vanity Fair, published days after Styles’ conversation with Rolling Stone, Wilde also defended their relationship, and denied rumours that she started dating Styles while she was still with Suedikis, who she was engaged to for seven years and shares two children, Otis, eight, and Daisy, six, with.

“The complete horses*** idea that I left Jason for Harry is completely inaccurate,” she said. “Our relationship was long over before I met Harry. Like any relationship that ends, it doesn’t end overnight.”

2023: Emily Ratajkowski

In March, the “Watermelon Sugar” singer and the model were seen kissing in Tokyo in a video captured by the DailyMail. In the clip, Styles and Ratajkowski kissed beside a car as John Legend’s song “Dope” played in the background.

While the pair haven’t said whether they’re in a relationship or not, some stars have shared their candid reactions to the rumoured couple. For example, Legend took to Instagram to poke fun at Styles and Ratajkowski, as he shared the PDA clip of them along with the caption: “Make out to #Dope…Everybody’s doing it.”

Julia Fox also weighed in on the dating rumours by commenting on Page Six’s Instagram post featuring a picture of Ratajkowski and Styles. In the comments of the post mentioning the pair’s kiss, the Uncut Gems star applauded the model, who she’s been close friends with, and wrote: “That’s my girl!”